Hello jmartinezs,
I looked at your model in R18.2 so I can't attach it because you can't open it (unless you can upgrade).
1) The Bolts are missing a split plane at the top of the nut to divide the shaft between a cylindrical face that is bonded to the nut and another face that is between the nut and the head to apply the Bolt Pretension to that face (not the body).
When I tried this on your geometry, I found that I can't apply the Bolt Pretension to the face because it is not cylindrical, it is a B-Surface. You need to delete the bolt bodies and recreate them with cylindrical faces.
If you have SpaceClaim, you can go to the Repair tab and use Simplify on the three bolts, but that will probably break everything else in your model.
Here is the result.
2) This should be a 2 step analysis. In step 1, the bolt pretension load is applied, while the remote displacement of the tip is held at zero. In step 2, the bolt pretension is locked and the remote displacement tip is ramped up. Step 2 should have Auto Time Stepping and 10 Initial and Minimum substeps as a first try.